Not exactly 5, but these really stand out in my mind today
1952 DRC RC
1969 Rousseau Chambertin
1971 DRC RSV
1989 Beaucastel
1830 Quinta do Serrado Malvasia
From what I remember at this moment. It will change if I’m asked the same question a month from now–not because I will have drank a wine that would infiltrate the list, but because I’ll remember different ones.
1970 Palmer
1996 Salon
2001 Muller-Catoir Haardter Burgergarten Riesling Spatlese #2134
1988 Climens
1990 G. Mascarello Barolo Monprivato
Five out of thousands of bottles is hard. How about…
1984 Ridge Monte Bello
1964 Clos Fourtet Justerini & Brooks bottled
1970 Jaboulet Hermitage La Chapelle
1985 Jaboulet Hermitage La Chapelle
1974 Sutter Home Deaver Vineyard
1970 Phelan Segur, my first real wine
1970 Latour, my first real great wine
1983 Grand cru les clos Rene Dauvisset
2002 Shafer HS
1996 Krug
I’ve been posting notes in CT for the last 5 years. It turns out I’ve rated exactly 5 bottles 100 points in that time:
1982 Château Margaux
1989 Giacosa Rionda Riserva (twice)
2001 Bruno Giacosa Barolo Riserva Le Rocche del Falletto
1961 Bruno Giacosa Barbaresco Riserva Speciale
The first wine I ever rated 100 points was the 1958 Bartolo Mascarello Barolo Riserva, so that should be on the list.
I noticed I did rate the 1971 Moët & Chandon Champagne Cuvée Dom Pérignon Oenothèque 99 points (as well as a few more Giacosas).
Looking further back, I see I once gave 100 points to a 1982 Pichon Longueville Comtesse de Lalande, a 1982 Leoville-Las Cases, a 1994 Dominus Estate, a 1990 Château Margaux, and a 1978 Bruno Giacosa Barbaresco Riserva Santo Sfefano. But to put these in context, I have 3 times given the 1989 Giacosa Rionda Riserva a score of 102 points. 
Many of these were at blind tastings.
What’s interesting to me is the high number of Bordeaux on these lists versus the relative paucity of Bordeaux discussion on this board. Has Bordeaux just gotten too expensive and too boring in recent years?
So many wines I have never tried are on the thread above me. Here is the list of my greatest wines that have really rocked my world.
2007 Joseph Phelps Insignia
2006 Cabot Vineyards Syrah Kimberly’s
2005 Château Gazin Rocquencourt
2010 Bodegas El Nido Jumilla Clio
2005 Kongsgaard Cabernet Sauvignon
It’s all been down hill for the last 25 years or so:
1955 Mouton Rothschild (in the late 1980’s)
1947 Clos des Lambrays (from magnum, in the late 1980’s)
1982 Domaine Vincent Leflaive Puligny-Montrachet Les Pucelles (from a 375 ml, in the late 1980’s)
1978 Domaine des Varoilles Bonnes Mare (in the late 1980’s)
1970 Robert Mondavi Unfined and Unfiltered Cabernet Sauvignon (in the late 1980’s)
1929 Vogue Musigny
1945 Vogue Musigny
1990 Leroy Musigny
1986 Ramonet Montrachet
1978 Arnoux Suchots or 1993 Coche Corton Charlemagne
In no particular order:
1947 Huet Le Haut Lieu
1989 Huet Cuvée Constance
1959 Lafite
1959 Haut-Brion
1997 Clos Rougeard Les Clos
The first four came to mind immediately. There were a lot of candidates for the fifth spot, but I can’t remember being as dumbstruck by a wine as I was by the Clos Rougeard in 2012. If kids knew the kind of high one can get huffing great Saumur-Champigny, spray paint manufacturers would be going out of business.
I had this wine about 15 years ago, it was gone (oxidized) about 2 mins after the cork was pulled.
Dunno, but here were some memorable ones:
'78 Rayas
'90 Chave
'89 La Mission
'59 Mouton
'82 Mouton
Ask me on a different day and I’ll give you a different set of 5.
Ben
In no particular order…
I think i paid $30 for a half bottle of 1970 latour, so i think its just out of reach nowadays. I would love a 2000 latour or lafite but cannot justify $1000
Top 5 greatest wines:
1999 Domaine de la Romanée-Conti Romanée-Conti
1990 Domaine de la Romanée-Conti Romanée-Conti
1945 Mouton Rothschild
1978 Domaine de la Romanée-Conti Romanée-Conti
1971 Domaine de la Romanée-Conti La Taché
No Nacional ?
The 1996 Nacional was my second tier. Would have been in competition for Top Ten, but not Top Five. And that’s not even one of their best. I tried to pick up a bottle of the 1963 at auction, but someone made a crazy bid and I lost it.
It’s really not that bad here relative to Bordeaux. First three pages have 10 threads about Bordeaux and more that have Bordeaux in the content. Enough content for us Bdx lovers to be interested (granted, I follow other wines and threads as well). I’m not surprised that there are so many Bdx on the lists of top 5s as a mature classified growth is a thing of beauty, some quite revelatory.
Off the top of my head:
1994 Dominus (on release, later bottles not quite as mind-blowing)
1991 Dominus (last year, the best but last of my stash, this has years left if you have some)
1990 Jaboulet La Chapelle (very uneven: only one out of three was anywhere near this level)
1990 Pichon Baron (twice, both times great)
1994 Zind-Humbrecht Rangen Tokay Pinot Gris (last week!)
Some Pegau and Clos Des Papes should be on this list. Geez, the 2006 Clos Des Papes I had on Sunday was stunning.